The Smiley rearrangement is an organic reaction and reordering reaction. This is an intramolecular nucleophilic aromatic substitution of the type:
in which X in arene compounds may be sulfones, sulphides, ether or substituents capable of releasing from arenas that carry a negative charge. Terminal functional groups at the end of the Y chain are able to act as strong nucleophiles such as alcohols, amines or thiols.
As with other nucleophilic aromatic substitutions, the arena requires activation by the electron-withdrawing group preferably in the aromatic ortho position.
In one modification called Truce-Smiles rearrangement, the incoming nucleophile is strong enough that the arene does not require this additional activation, for example when the nucleophile is an organolytic. This reaction is exemplified by the conversion of aryl sulphon to sulfinic acid by the action of n -butyllithium:
This particular reaction requires the interaction of a group alkyllithium group to a sulfon group similar to that of a directed ortho metallization.
The related conceptual reactions are Chapman's arrangement.
The radical version of Smiles rearrangement is reported by Stephenson in 2015.
Hayashi's rearrangement can be considered a cation partner of Smiles rearrangement.
Video Smiles rearrangement
External links
- Articles in Organic synthesis: Org. Synth. 2007 , 84, p. 325-333.
Maps Smiles rearrangement
References
Source of the article : Wikipedia
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